메뉴 건너뛰기




Volumn 12, Issue 13, 2010, Pages 3014-3017

Diastereoselective intramolecular additions of allyl- and propargylsilanes to iminium ions: Synthesis of cyclic and bicyclic quaternary amino acids

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; ALLYL COMPOUND; AMINO ACID; IMINE; ION; SILANE DERIVATIVE;

EID: 77954094926     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1010246     Document Type: Article
Times cited : (24)

References (49)
  • 11
    • 77954124741 scopus 로고    scopus 로고
    • For intermolecular diastereoselective alkyl additions to the iminic carbon in related molecules, see
    • For intermolecular diastereoselective alkyl additions to the iminic carbon in related molecules, see
  • 15
    • 77954117862 scopus 로고    scopus 로고
    • For reviews, see
    • For reviews, see
  • 20
    • 77954101643 scopus 로고    scopus 로고
    • For our previous asymmetric syntheses of 2,2-difluoro-1-ACACs, see
    • For our previous asymmetric syntheses of 2,2-difluoro-1-ACACs, see
  • 25
    • 77954103804 scopus 로고    scopus 로고
    • Imino lactones 4a, b were prepared by condensation of the corresponding α-keto esters with (R)-phenylglycinol; see ref 3a
    • Imino lactones 4a, b were prepared by condensation of the corresponding α-keto esters with (R)-phenylglycinol; see ref 3a.
  • 26
    • 77954114643 scopus 로고    scopus 로고
    • The pure cis isomer of 5a was also obtained by a different synthetic route based on the partial hydrogenation of a triple bond, and its subsequent cyclization to 6a afforded the same stereochemical result as the trans / cis mixture
    • The pure cis isomer of 5a was also obtained by a different synthetic route based on the partial hydrogenation of a triple bond, and its subsequent cyclization to 6a afforded the same stereochemical result as the trans / cis mixture.
  • 27
    • 77954102718 scopus 로고    scopus 로고
    • The diastereomeric ratio was measured by HPLC. Only three out of four diastereoisomers were detected both by HPLC and NMR
    • The diastereomeric ratio was measured by HPLC. Only three out of four diastereoisomers were detected both by HPLC and NMR.
  • 32
    • 77954125553 scopus 로고    scopus 로고
    • N -Allylation of 6a was also tested but resulted in a complex mixture of products under several reaction conditions
    • N -Allylation of 6a was also tested but resulted in a complex mixture of products under several reaction conditions.
  • 33
    • 77954138562 scopus 로고    scopus 로고
    • Cis -fused 2-azabicyclo[4.3.0]nonane-1-carboxylic acids were previously prepared and used as scaffolds for β-turn mimics, see
    • Cis -fused 2-azabicyclo[4.3.0]nonane-1-carboxylic acids were previously prepared and used as scaffolds for β-turn mimics, see
  • 38
    • 77954097405 scopus 로고    scopus 로고
    • For a recent article combining both iminium ion additions and gold-catalyzed hydroaminations, see
    • For a recent article combining both iminium ion additions and gold-catalyzed hydroaminations, see
  • 40
    • 77954117596 scopus 로고    scopus 로고
    • In contrast, a similar hydroamination protocol was unsuccessful using vinylic derivative 6a
    • In contrast, a similar hydroamination protocol was unsuccessful using vinylic derivative 6a.
  • 41
    • 77954108803 scopus 로고    scopus 로고
    • For a previous synthesis of (+)- 20, see
    • For a previous synthesis of (+)- 20, see
  • 42
    • 63749121681 scopus 로고    scopus 로고
    • For the synthesis of other bicycloproline derivatives, see:
    • Ranatunga, S.; Del Valle, J. R. Tetrahedron Lett. 2009, 50, 2464-2466 For the synthesis of other bicycloproline derivatives, see:
    • (2009) Tetrahedron Lett. , vol.50 , pp. 2464-2466
    • Ranatunga, S.1    Del Valle, J.R.2
  • 46
    • 77954106556 scopus 로고    scopus 로고
    • For examples, see
    • For examples, see


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.